Winter Garden vacation rentals

We found 33,606 vacation rentals — enter your dates for availability

Discover a selection of 7 condos and other vacation rentals in Winter Garden that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a pool. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Winter Garden

Showing deals for:Jun 19 - Jun 26

Image gallery for Stylish and Cozy Pool Home near Disney in a Gated Community

Newly surfaced pool facing conservation area!
9.4 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

Stylish and Cozy Pool Home near Disney in a Gated Community

Kissimmee

8% off
Price is $479
$3,352 for 7 nights
All fees included
Stylish and Cozy Pool Home near Disney in a Gated Community

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Find out more about Winter Garden

Why visit Winter Garden

  • Charming Downtown: Stroll along Plant Street to experience local shops, eateries, and a vibrant atmosphere.
  • Proximity to Theme Parks: Enjoy easy access to the nearby Walt Disney World Resort for thrilling adventures.
  • Outdoor Activities: Explore local gardens, citrus groves, and the scenic Green Mountain Getaway for outdoor fun.
  • Art and Culture: Discover unique art galleries that add a creative touch to your visit.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including cozy homes and spacious villas.

Popular types of accommodation in Winter Garden

Planning a getaway to Winter Garden? The excitement begins with selecting the perfect place to stay. Discover a range of popular vacation rentals, including houses, villas, and condos. Whether you're searching for FL vacation rentals, apartment rentals, or spacious townhomes, Winter Garden has options to suit every traveler. Enjoy your stay in a cozy guest house or a charming FL home for rent, and make the most of your vacation experience.

  • Houses: These spacious homes are the top choice for visitors to Winter Garden, perfect for families or groups seeking comfort and privacy.
  • Villas: Luxurious and spacious, villas offer an upscale experience with beautiful amenities for a relaxing getaway.
  • Condos: Ideal for those wanting convenience, condos provide modern living spaces close to attractions.
  • Apartments: Affordable and practical, apartments are great for solo travelers or couples looking for a home-away-from-home vibe.
  • Cottages: Quaint and charming, cottages offer a cozy atmosphere for a peaceful retreat.**

Top attractions in and around Winter Garden

Winter Garden, Florida, is a fantastic destination for families and entertainment seekers alike. Visitors can enjoy a variety of attractions, including theme parks, golf courses, and arts centers. The area offers a blend of cultural and outdoor experiences, with local gardens, mini golf, citrus groves, and the nearby Walt Disney World Resort. Art galleries also add a creative touch to your adventure, making Winter Garden a well-rounded vacation spot.

  • Orange County National Golf Club: A premier golf destination offering lush greens and a welcoming atmosphere, perfect for families and golf enthusiasts alike. Enjoy excursions tailored to all skill levels with friendly staff ensuring a memorable experience.
  • Walt Disney World® Resort: Located 10 miles away, this iconic theme park offers magical entertainment for families, featuring thrilling rides, beloved characters, and enchanting shows that create unforgettable memories.
  • AdventHealth Winter Garden: More than a medical center, it provides a family-friendly environment with a focus on community health and wellness, making it a trusted resource for locals and visitors alike.

Things to do recommended for couples

For a romantic getaway in Winter Garden, consider the luxurious ambiance of Windermere Country Club, just 4 miles away. Alternatively, enjoy the exclusivity of Alaqua Country Club, 17 miles from Winter Garden, or try the charming Mount Dora Lawn Bowling Club, located 16 miles from town.

Things to do recommended for families

Families visiting Winter Garden can explore the fun at the Central Florida Railroad Museum, enjoy outdoor activities at Lake Apopka, and visit the vibrant Winter Garden Farmers Market for fresh produce and local crafts. It's a perfect blend of culture and adventure for everyone.

Things to do recommended for groups

Groups visiting Winter Garden can enjoy a stroll through the picturesque Downtown Historic District, savor local flavors at the farmer's market, and take a scenic bike ride along the West Orange Trail, offering beautiful views and a chance to connect with nature.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter Garden

If you're traveling with a group, with family, bringing pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Winter Garden with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winter Garden with young kids: Traveling with young children can be quite demanding. It’s essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winter Garden: For many, a family vacation wouldn’t be the same without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Garden: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Winter Garden

Your vacation in Winter Garden, Florida promises a delightful blend of family-friendly fun and relaxing vibes. Explore the charming downtown area, stroll along Plant Street, and indulge in the local atmosphere. Nearby, the Green Mountain Getaway offers excursions perfect for sunny weather. Whether you're seeking entertainment or a peaceful retreat, Winter Garden and its surrounding neighborhoods provide an inviting escape for all types of travelers.

  • Orlando: Orlando, located 13 miles from Winter Garden, is synonymous with family fun and entertainment. This vibrant city is home to world-renowned theme parks such as Walt Disney World and Universal Studios, making it a prime destination for thrill-seekers and families alike. Beyond the parks, visitors can explore the cultural side of Orlando at the Orlando Museum of Art or catch a show at the Dr. Phillips Center for the Performing Arts. Shopping enthusiasts will enjoy the diverse array of retail options ranging from high-end boutiques to sprawling malls. Orlando’s unique blend of attractions ensures a memorable experience for all types of travelers.
  • Ocoee: Just 3 miles from Winter Garden, Ocoee offers a charming blend of family-friendly activities and outdoor adventures. Known for its lovely parks and recreational areas, visitors can enjoy hiking, biking, and picnicking in the scenic landscape. The city also features shopping centers and a variety of dining options, catering to all tastes. With close proximity to popular attractions like theme parks and sports facilities, Ocoee is an excellent spot for those looking to unwind while still having access to exciting entertainment.
  • Vista del Lago: Nestled around Winter Garden, Vista del Lago is a delightful neighborhood that provides a family-oriented and city-themed experience. Residents and visitors can enjoy the local shopping areas and malls, making it easy to find unique items and dining options. The neighborhood is also close to beautiful lakes, perfect for leisurely strolls or picnics. With nearby attractions like theme parks and film studios, Vista del Lago offers a serene environment while keeping the excitement of city life within reach.

Best time to go to Winter Garden

If you're planning a trip to Winter Garden, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January to February and September, while off-peak times, like May, August and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January59.9°F (15.5°C)Light RainMostly SunnySlightly HighAverage
February63.9°F (17.7°C)Light RainMostly SunnySlightly HighSlightly Low
March67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
April72.5°F (22.5°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnySlightly LowAverage
June81.0°F (27.2°C)Moderate RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowAverage
September80.2°F (26.8°C)Moderate RainMostly SunnySlightly HighSlightly Low
October74.8°F (23.8°C)Light RainMostly SunnySlightly LowSlightly Low
November67.8°F (19.9°C)Light RainMostly SunnyAverageAverage
December63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next journey? One effective strategy is to stay flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To help you find the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume previous ones, or organize your travel arrangements. You’ll find your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The friendly area of Winter Garden awaits your stay

Experience the unique character of Winter Garden with a stay in a vacation home rental. Well-liked for its theme park, shopping and water park, this city is both welcoming and relaxing. Walt Disney World® area and Walt Disney World® Resort are just a couple of the must-sees. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

West Orange history and wild rides in Winter Garden

Quaint little Winter Garden has its own clutch of intriguing attractions. There's the Winter Garden Heritage Foundation, which chronicles the rich culture of West Orange. There's the Central Florida Railroad Museum with its old tracks and platforms. There's the Garden Theatre, dating back to the 1930s. Winter Garden vacation rentals close to Walt Disney World offer a whole other bunch of delights. Rollercoasters and rides aplenty can be expected, from the sloshing wave pools of Typhoon Lagoon to the dusty savannahs of the wild Animal Kingdom and beyond.

Living like a local in Winter Garden

Walk your way around the old Downtown of Winter Garden to spy out the historic relics of its railroad past – you can even get guided tours of the place to really delve into the heritage. Then, make for the weekly farmer's market to shop for fresh fruit and Floridian produce in the company of locals, or hop between the independent cafes and microbreweries learning the ins and outs of bean roasting and beer tasting. When evening comes, the whole of Plant Street buzzes with life, whether that means summertime jazz sessions or fine-dining in the bistros there.

Exploring the natural features in Winter Garden

Whether you're an active traveler or just want to spend some time taking in the scenery, Winter Garden is a great spot to appreciate mother nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Hancock Park (7.9 mi / 12.7 km)
  • Bill Frederick Park (8 mi / 12.9 km)
  • Rock Springs Run (8.8 mi / 14.2 km)
  • Lake Louisa State Park (11.1 mi / 17.9 km)
  • Wekiwa Springs State Park (12.5 mi / 20.1 km)
  • Lake Eola Park (13 mi / 20.9 km)

Transportation to and around Winter Garden

The nearest airport is in Orlando Intl. Airport (MCO), located 19.3 mi (31 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is 20.8 mi (33.5 km) away.

Frequently asked questions

What is the best area to stay in Winter Garden, Florida, United States of America when booking a vacation rental?
One of the best areas to stay in Winter Garden, Florida, is the charming downtown district. This vibrant neighborhood offers a delightful mix of historic architecture and modern conveniences, creating a special environment for visitors. You'll find a variety of vacation rental options here, ranging from cozy cottages to spacious homes, allowing you to choose what best suits your needs.

Downtown Winter Garden is particularly known for its scenic West Orange Trail, great for walking, jogging, or biking. Additionally, the beautiful Garden Theatre hosts a range of performances and events, making it a cultural hub for entertainment. The area also features an array of delightful restaurants and shops, ensuring you have everything you need right at your doorstep.

Another great option is the neighborhoods surrounding the beautiful Lake Apopka. This area offers a more serene environment, with ample opportunities for outdoor activities like fishing, kayaking, or simply enjoying the picturesque views. There are numerous properties available here, many with easy access to the lake and lush green spaces.
How much does it cost to rent a vacation home in Winter Garden?
Prices for vacation rentals in Winter Garden vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Garden to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Garden vacation house rentals?
You can find great discounts on house rentals in Winter Garden on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Winter Garden?
In Winter Garden, condos are the most popular type of vacation rental, with about 69 available throughout the area. These condos are often located in vibrant neighborhoods close to local attractions such as the historic downtown area and the West Orange Trail, making them convenient for exploring the region. Most condos come equipped with modern amenities, including full kitchens, spacious living areas, and access to community features like pools and fitness centers.

Apartments also see significant popularity, with around 26 options for travelers. These typically offer cozy living spaces, kitchen facilities, and often include amenities such as laundry services and parking.

For those seeking more space, there are approximately 24 vacation houses available, which usually feature multiple bedrooms, private outdoor areas, and family-friendly layouts. Cottages and villas, though fewer in number with 10 each, provide charming and unique accommodations, often set in quieter parts of Winter Garden.
Are there any family house rentals in Winter Garden?
In Winter Garden, Florida, there are numerous family-friendly vacation rentals available, with around 98 options scattered throughout the area. This charming city, known for its picturesque downtown and proximity to various attractions, offers homes that cater to families perfectly. Many of these properties include spacious living areas, fully equipped kitchens ideal for preparing meals together, and outdoor spaces where children can play or families can enjoy barbecues.

Visitors will find amenities like Wi-Fi, laundry facilities, and air conditioning, which contribute to a comfortable stay. The neighborhoods around Winter Garden are also close to popular spots such as the West Orange Trail, great for biking and walking, and the beautiful Lake Apopka, which offers opportunities for fishing and birdwatching.
Can I rent a vacation home with a pool or hot tub in Winter Garden?
In Winter Garden, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 93 options to choose from. This charming town, located near Orlando, offers a variety of neighborhoods where these properties can be found, including the picturesque Historic Downtown area known for its quaint shops and restaurants, as well as the more spacious suburban neighborhoods that provide a tranquil retreat.

Travelers can expect a range of amenities in these rentals, including private pools, relaxing hot tubs, outdoor dining areas, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a fun and comfortable stay.
Can I find long-stay vacation rentals in Winter Garden?
A long-stay vacation rental in Winter Garden is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winter Garden?
In Winter Garden, travelers will find a variety of pet-friendly house rentals that cater to families and groups looking for a comfortable stay. With around 67 options available, these rentals typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like patios or gardens where pets can enjoy the fresh air.

The charming downtown area offers a mix of shops and restaurants, and the nearby West Orange Trail is great for walking or biking with pets, providing a scenic route through the lush landscape. Additionally, the proximity to parks and recreational areas enhances the appeal for pet owners, ensuring both relaxation and outdoor activities are easily accessible during their visit.
Are there any remote work vacation rentals in Winter Garden?
In Winter Garden, Florida, there are plenty of remote work vacation rentals available, with around 131 options for travelers seeking to combine work and leisure. This charming town offers a variety of accommodations featuring essential amenities for remote work, such as free Wi-Fi in both public areas and individual rooms, ensuring a reliable connection for productivity. Many properties also include designated office spaces, great for focused work sessions.

The area is known for its beautiful historic downtown, where visitors can enjoy local shops, cafes, and restaurants, providing a pleasant atmosphere for breaks or after-work relaxation. Additionally, outdoor spaces such as parks and the West Orange Trail offer opportunities for walking, biking, or simply unwinding in nature. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Garden vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Garden with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Garden?
In Winter Garden, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals. Many rentals also offer onsite parking for added convenience. Guests can enjoy a coffee or tea maker in their accommodations, great for starting the day with a warm beverage. Additionally, several properties feature balconies where visitors can relax and take in the surroundings. For those looking for a touch of luxury, hot tubs are available in some rentals, providing a great way to unwind after a day of exploration.
When is the best time to visit Winter Garden for a vacation rental?
The best time to visit Winter Garden for a vacation rental is during the peak season from January to March. This period attracts a vibrant mix of travelers seeking to enjoy the area's charming downtown, lush gardens, and outdoor activities in pleasant weather. With temperatures typically ranging from the mid-50s to mid-70s Fahrenheit, this season provides a comfortable climate for exploring the scenic West Orange Trail and nearby parks.

September is also a popular month, as visitors can experience the tail end of summer with a relaxed atmosphere and fewer crowds. The warm temperatures, generally in the high 70s to low 90s Fahrenheit, make it superb for enjoying outdoor events and local markets, while still allowing for some peaceful moments in the community's parks and gardens.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a lovely transition into fall, with mild weather and a chance to enjoy the beauty of the area without the hustle and bustle of peak tourist activity. You can explore the historic downtown area at a more leisurely pace and discover local dining gems.

Ultimately, your choice will depend on whether you prefer the lively energy of the peak season or the serene charm of the shoulder months.
How early should I book a Winter Garden vacation rental?
Book your Winter Garden vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winter Garden, Florida, United States of America?
In Winter Garden, visitors can explore the charming downtown area, which features a variety of shops, restaurants, and the historic Winter Garden Theatre. The West Orange Trail, a popular destination for walking and biking, runs through the city and offers scenic views and access to the outdoors. Nearby, the Plant Street Market is a vibrant hub for local vendors, craft beer, and fresh produce, making it a great spot to experience the local culture. For nature enthusiasts, the nearby Lake Apopka provides opportunities for birdwatching and enjoying the natural beauty of the region.
Can I change or cancel my Winter Garden home rental booking on Vrbo?
To find Winter Garden vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winter Garden vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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